WO2008107096A1 - Diaminopyrimidine als fungizide - Google Patents

Diaminopyrimidine als fungizide Download PDF

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Publication number
WO2008107096A1
WO2008107096A1 PCT/EP2008/001503 EP2008001503W WO2008107096A1 WO 2008107096 A1 WO2008107096 A1 WO 2008107096A1 EP 2008001503 W EP2008001503 W EP 2008001503W WO 2008107096 A1 WO2008107096 A1 WO 2008107096A1
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WIPO (PCT)
Prior art keywords
amino
oxo
dihydro
och
methyl
Prior art date
Application number
PCT/EP2008/001503
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German (de)
English (en)
French (fr)
Inventor
Jörg Nico GREUL
Oliver Gaertzen
Ralf Dunkel
Amos Mattes
Stefan Hillebrand
Ulrike Wachendorff-Neumann
Peter Dahmen
Arnd Voerste
Peter Schreier
Pierre-Yves Coqueron
Original Assignee
Bayer Cropscience Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Priority to EA200901187A priority Critical patent/EA015174B1/ru
Priority to AU2008224150A priority patent/AU2008224150A1/en
Priority to BRPI0808433-5A priority patent/BRPI0808433A2/pt
Priority to EP08716043A priority patent/EP2129222A1/de
Priority to MX2009008700A priority patent/MX2009008700A/es
Priority to CA002679488A priority patent/CA2679488A1/en
Priority to JP2009551126A priority patent/JP2010520160A/ja
Priority to US12/529,612 priority patent/US20100081679A1/en
Publication of WO2008107096A1 publication Critical patent/WO2008107096A1/de
Priority to IL200122A priority patent/IL200122A0/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to cyclopropyl-substituted diaminopyrimidines and their use for controlling unwanted microorganisms.
  • cyclopropyl-substituted diaminopyrimidines are already known as pharmaceutically active compounds (see, for example, US Pat. No. 04/256145, WO 05/016893, WO 05/013996, WO 04/056786, WO 04/056807, WO 03/076437, WO 02/096888 , WO 02/004429), but not their surprising fungicidal activity.
  • the invention relates to the use of compounds of the formula (I) as fungicides,
  • X 1 is nitrogen or CR 3
  • X 2 is nitrogen or CR 4
  • each two adjacent radicals R 2 , R 3 or R 4 optionally via R 12 or R 13 , together form a 3- to 7-membered, unsubstituted or substituted, saturated or unsaturated cycle, the no or may contain up to four heteroatoms selected from N, O and S, with two oxygen atoms not adjacent.
  • R 6 is hydrogen, unsubstituted or substituted benzyl, unsubstituted or substituted C r C 8 alkyl, unsubstituted or substituted C 1 -C 4 -alkylC (OO), C 1 -C 4 -alkyl OC (OO), unsubstituted or substituted ci C 4 alkoxy (Ci-C 4) alkyl, unsubstituted or substituted Ci-C 6 -alkenyl, unsubstituted or substituted Ci-C 6 -alkynyl, CrC ⁇ alkylsulfinyl, C r C 6 alkylsulfonyl, C 3 -C 8 cycloalkyl ; C r C 6 haloalkyl, C r C 4 haloalkylsulfinyl, C, -C 4 - haloalkylsulphonyl, halo-Ci-C4-alkoxy-Ci
  • R 1 A represents hydrogen, C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 - cycloalkyl, (C r C 4 - Alkoxy) carbonyl, (C 3 -C 6 -alkenyloxy) carbonyl, (C 3 -C 6 -alkynyloxy) carbonyl or cyano,
  • R 7 is hydrogen, cyano, methyl, CF 3 , CFH 2 or CF 2 H
  • R 8 is fluoro, chloro, bromo, iodo, cyano, methyl, C r C 3 haloalkyl
  • R 11 is identical or different hydrogen, fluorine, chlorine, bromine, unsubstituted or substituted C r C 8 alkyl, C r C 8 alkyloxy, C 3 -C 8 cycloalkyl, C, -C 8 haloalkyl, Ci-C 4- trialkyl-silyl, unsubstituted or substituted aryl, unsubstituted or substituted cyclopropyl
  • R 12 is identical or different hydrogen, unsubstituted or substituted CrC 8 alkyl, unsubstituted or substituted Ci-C 8 haloalkyl, unsubstituted or substituted C 3 -C 6 - cycloalkyl, Ci-C4-trialkyl-silyl, unsubstituted or substituted C C 2 -C 6 -alkenyl, unsubstituted or substituted C 3 -C 6 -alkynyl, unsubstituted or substituted aryl, C 1 -C 4 -alkoxy (C 1 -C 4 ) -alkyl, unsubstituted or substituted benzyl or a 3 to 7-membered unsubstituted or substituted, saturated or unsaturated cycle which may contain no or up to four heteroatoms selected from N, O and S, where two oxygen atoms are not adjacent,
  • two R 12 may be a 3 to 7 membered, unsubstituted or substituted, saturated or unsaturated cycle containing up to four further heteroatoms selected from N, O and S may contain, wherein two oxygen atoms are not adjacent form.
  • two R 12's can be a 3 to 7 membered, unsubstituted or substituted, saturated or unsaturated cycle containing up to four further heteroatoms selected from N , O and S, wherein two oxygen atoms are not adjacent form.
  • R 13 is identical or different unsubstituted or substituted C r C 8 alkyl, unsubstituted or substituted C r C 8 haloalkyl, C r C 4 -trialkyl-silyl, unsubstituted or substituted substituted C ö alkenyl, unsubstituted or substituted Ci-C ⁇ -alkynyl, unsubstituted or substituted C 3 -C 6 -cycloalkyl, unsubstituted or substituted aryl, Ci-C4 alkoxy (Ci- C4) alkyl, unsubstituted or substituted Benzyl or a 3- to 7-membered, unsubstituted or substituted, saturated or unsaturated cycle which may contain no or up to four heteroatoms selected from N, O and S, where two oxygen atoms are not adjacent,
  • R 13 may form a 3 to 7 membered, unsubstituted or substituted, saturated or unsaturated cycle which may contain up to four further heteroatoms selected from N, O and S wherein two oxygen atoms are not adjacent.
  • R 14 is identical or different hydrogen, fluorine, chlorine, bromine, unsubstituted or substituted Ci-Cg-alkyl, QQ-alkyloxy, C 3 -C 8 -cycloalkyl, C r C 8 -haloalkyl, C r C 4 -trialkyl-silyl .
  • Compounds of the formula (I) are very suitable for controlling unwanted microorganisms. Above all, they show a strong fungicidal activity and can be used both in crop protection and in the protection of materials.
  • the compounds of the formula (I) can be used both in pure form and as mixtures of various possible isomeric forms, in particular of stereoisomers, such as E and Z, threo and erythro, and optical isomers, such as R and S isomers or Atropisomers, but optionally also of tautomers. Both the E and the Z isomers, as well as the threo and erythro, and the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms claimed.
  • stereoisomers such as E and Z, threo and erythro
  • optical isomers such as R and S isomers or Atropisomers
  • the compounds of the invention are generally defined by the formula (I).
  • X 1 is nitrogen or CR 3
  • X 2 is nitrogen or CR 4
  • A is C (R 14 ) 2 or a direct bond
  • R 1 to R 5 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano,
  • 2,3-dihydro-1H-benzimidazol-5-yl) amino (2-oxo-1,3-benzoxathiol-5-yl) -amino, (2-oxo-2,3-dihydro-1H-indole-5- yl) amino, 2-oxo-2,3-dihydro-l, 3-benzoxazol-5-yl) amino, (2-ethyl-l, 3-benzoxazol-5-yl) amino, 2-oxo-l, 2 , 3,4-tetrahydroquinolin-6-yl) amino, (3-oxo-3,4-dihydro-2H-l, 4- benzoxazin-6-yl) amino, (2-oxo-2,3-dihydrol, 3-benzoxazol-6-yl) amino, 3-oxo-1,3-dihydro-2-benzofuran-5-yl) -amino.
  • R 1 A represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or cyano
  • R 7 is hydrogen, cyano, methyl, CF 3 , CFH 2 or CF 2 H
  • R 8 is fluoro, chloro, bromo, iodo, cyano, methyl, CF 3 , CCl 3 , CFH 2 or CF 2 H
  • R 12 is the same or different hydrogen, unsubstituted or substituted C r C 6 alkyl, unsubstituted or substituted Ci-C 6 haloalkyl, unsubstituted or substituted C 3 -C 6 - cycloalkyl, Ci-C 4 -Trialkyl-silyl, unsubstituted or substituted C 2 -C 4 -alkenyl, unsubstituted or substituted C 3 -C 4 alkynyl, unsubstituted or substituted phenyl, C r C 4 - alkoxy (!
  • alkyl unsubstituted or substituted benzyl or a 3- to 7 a lower, unsubstituted or substituted, saturated or unsaturated cycle which may contain no or up to four heteroatoms selected from N, O and S, wherein two oxygen atoms are not adjacent
  • two R 12 may be a 3 to 7 membered, unsubstituted or substituted, saturated or unsaturated cycle containing up to four further heteroatoms selected from N, O and S may contain, wherein two oxygen atoms are not adjacent form.
  • two R 12's can be a 3 to 7 membered, unsubstituted or substituted, saturated or unsaturated cycle containing up to four further heteroatoms selected from N , O and S, wherein two oxygen atoms are not adjacent form.
  • R 13 is identical or different unsubstituted or substituted Ci-C ö alkyl, unsubstituted or substituted C r C 6 haloalkyl, C 1 -C 4 -TrIaIlCyI-silyl, unsubstituted or substituted Ci-C 4 alkenyl, unsubstituted or substituted C -C 4 alkynyl, unsubstituted or substituted C 3 -C 6 -cycloalkyl, unsubstituted or substituted aryl, Ci-C 4 alkoxy (C r C4) alkyl, unsubstituted or substituted benzyl or a 3- to 7-membered, unsubstituted or a substituted, saturated or unsaturated cycle which may contain no or up to four heteroatoms selected from N, O and S, where two oxygen atoms are not adjacent,
  • R 13 may form a 3 to 7 membered, unsubstituted or substituted, saturated or unsaturated cycle which may contain up to four further heteroatoms selected from N, O and S wherein two oxygen atoms are not adjacent.
  • R 14 is identical or different hydrogen, fluorine, chlorine, bromine, unsubstituted or substituted Ci-Cg-alkyl, Q-Cg-alkyloxy, C 3 -C 8 -cycloalkyl, C r C 8 -haloalkyl, C r C 4 -trialkyl - SUyI,
  • X 1 is nitrogen or CR 3
  • X 2 is nitrogen or CR 4
  • A is C (R 14 ) 2 or a direct bond
  • R 1 to R 5 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano,
  • R 7 is hydrogen, cyano, methyl, CF 3 , CFH 2 or CF 2 H
  • R 8 is fluoro, chloro, bromo, iodo, cyano, methyl, CF 3 , CCl 3 , CFH 2 or CF 2 H
  • R 10 is hydrogen, OH, OMe, OEt, OPr, OZ-Pr, OBu, OFBU, OzBu, OsBu, O-pentyl, O "eoPentyl, Me, Et, Pr, z 'Pr, Bu, tBu, / Bu , sBu, pentyl, "eoPentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, COOH, COOMe, COOEt, COOPr, COOZ-Pr, COOBu, COOzBu, COOsBu, COOfBu, COO-pentyl, COOvo-pentyl, phenyl, 2-chlorophenyl, benzyl, COOMe, COEt, COMe, COPr, COzsoPr, COBu, COfBu, COisoBu, COsBu, CO-pentyl, COneoPentyl
  • R 11 is identical or different hydrogen, fluorine, chlorine, bromine,
  • R 14 is the same or different hydrogen, methyl, ethyl, cyclopropyl, cyclobutyl, cyclopentyl, isopropyl
  • X 1 is nitrogen or CR 3
  • X 2 is nitrogen or CR 4
  • R 1 to R 5 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OzsoPr, OBu, OsecBu, OisoBu, OtertBu, (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OCH 3 , O -cylopentyl, OCF 3 , OCF 2 H, OCF 2 CF 3 , OCF 2 CF 2 H OCH 2 CH 2 N (C 2 Hs) 2, OCH (CH 3 ) CH 2 OCH 3 , SH, SMe, SPh, SEt, SPr, SzsoPr, SBu, SsecBu, SisoBu, StBu, SPentyl, SsecPentyl, SrceoPentyl, SOctyl, SCF 3, SCF 2 H, SOMe, SO-Et, SO-Pr, SOzsoPr, SOBU SOsecBu,
  • R 7 is hydrogen, cyano, methyl, CF 3 , CFH 2
  • R 8 is fluoro, chloro, bromo, iodo, cyano, methyl, CF 3 , CCl 3 , CFH 2 or CF 2 H
  • R 9 is hydrogen, Me, CH 2 OCH 3 , COMe, COOMe, COOEt, COOtertBu, COCF 3, benzyl, 4-methoxybenzyl,
  • R 10 is hydrogen, OEt, COOEt, 2-chlorophenyl, COOMe, COEt, COMe,
  • R 1 ' is the same or different hydrogen, fluorine, chlorine
  • X 1 is nitrogen or CR 3
  • X 2 is nitrogen or CR 4
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 1 to R 5 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano,
  • NHCOCH 2 OCH 3 NHCO (CH 2 ) 2 OCH 3 , N (CH 3 ) COCH 3 , N (C 2 H 5 ) COCH 3 , N (CH 3 ) COC (CH 3 ) 3 , N (C 2 H 5 ) COOCH 3 , NHCHO, N (CH 3 ) CHO, NMe 2 , NEt 2 , NHMe, NH 2 , NHtertBu, NHEt, NHPr, NHwoPr, NHBu, NH / soBu, NHsecBu, cyclopropylamino, NHCH (CH 3 ) CH 2 OCH 3 , NCH 3 COCH 3 , acetyl (cyclopropyl) amino, [(1-methylcyclopropyl) carbonyl] amino, morpholin-1-yl, methyl-4-ylmethyl, NHSO 2 CH 3 NHSOMe, NHSO 2 Me, NHSOCF 3 , NHSO 2 CF 3 ,
  • R 6 is hydrogen, Me, formyl, COMe, COOMe, COOEt, COOtertBu, COOBn, COCF 3, benzyl,
  • R 7 is hydrogen, methyl, CF 3 ,
  • R 8 is fluoro, chloro, bromo, iodo, cyano, methyl, CF 3 , CCl 3 , CFH 2
  • R 9 is hydrogen, Me,
  • R 10 is hydrogen, OEt, COOEt, 2-chlorophenyl R 1 'is the same or different hydrogen, fluorine, chlorine
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt
  • R 11 is H
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • X 1 is nitrogen or CR 3
  • X 2 is nitrogen or CR 4
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is CH 2 OPh
  • A is a direct bond, methylene or -CH (CH 3 ) - R 10 is hydrogen, Me, CF 3 , OEt, COOH, COOMe, COOEt, phenyl, benzyl, 2-chlorophenyl, 3-fluorophenyl, 3-bromophenyl, 3-trifluoromethylphenyl, 3-chlorophenyl, 3-methoxyphenyl, 4-methoxyphenyl, CH 2 OPh,
  • R 11 is identical or different hydrogen, fluorine, methyl, CF 3 , phenyl, OEt, SMe, 4-fluorophenyl, 4-methylphenyl,
  • both R 1 ' are simultaneously methyl or fluorine.
  • X 1 is CR 3 and
  • X 2 is CR 4 ,
  • X 1 is nitrogen
  • X 1 is CR 3 and X 2 is nitrogen
  • R 10 is H or Me
  • R l la ' b ' c is H
  • X 1 is CR 3 and
  • X 2 is CR 4 ,
  • R 6 is H, CHO, COCH 3 , COCF 3 ,
  • R 7 is H
  • R 9 is H, Me, CHO, COCH 3
  • R 1 is H
  • R 5 is H
  • R 1 is H
  • R 5 is H
  • X 1 is CR 3 and
  • X 2 is CR 4 ,
  • R 8 is chlorine, bromine, CF 3 ,
  • each two adjacent radicals R 2 , R 3 or R 4 optionally via R 12 or R 13 , together form a 3- to 7-membered, unsubstituted or substituted, saturated or unsaturated cycle, the no or may contain up to four heteroatoms selected from N, O and S, with two oxygen atoms not adjacent.
  • the invention also relates to compounds of the formulas (Ia), (Ib), (Ic), (Id), (Ie) and (If).
  • R 8a is chlorine, iodine, CFH 2 , CF 2 H or CCl 3 and
  • X 1 , X 2 , A, R 1 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are the abovementioned general, preferred, particularly preferred, very particularly preferred and in particular preferred meanings, as well as agrochemically active salts of these compounds are preferred.
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R, 1 1 0 is H, OEt
  • R 11 is H
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • both R 1 ' are simultaneously methyl or fluorine.
  • X 1 is nitrogen or CR 3
  • X 2 is nitrogen or CR 4
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is CH 2 OPh
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is hydrogen, Me, CF 3 , OEt, COOH, COOMe, COOEt, phenyl, benzyl, 2-chlorophenyl, 3-fluorophenyl, 3-bromophenyl, 3-trifluoromethylphenyl, 3-chlorophenyl, 3-methoxyphenyl, 4-methoxyphenyl, CH 2 OPh,
  • R 11 is identical or different hydrogen, fluorine, methyl, CF 3 , phenyl, OEt, SMe, 4-fluorophenyl, 4-methylphenyl,
  • both R 1 ' are simultaneously methyl or fluorine.
  • X 1 is CR 3 and
  • X 2 is CR 4 ,
  • X 1 is nitrogen
  • X 1 is CR 3 and
  • R 10 is H or Me
  • R 11 is H
  • X 1 is CR 3 and
  • X 2 is CR 4 ,
  • R 6 is H, CHO, COCH 3 , COCF 3 ,
  • R 7 is H
  • R 9 is H, Me, CHO, COCH 3
  • R 1 is H
  • R 5 is H
  • R 1 is H
  • R 5 is H
  • X 1 is CR 3 and
  • X 2 is CR 4 ,
  • R 8a is chlorine, the remaining substituents having one or more of the meanings mentioned above,
  • X lb is nitrogen or CR 3b .
  • R 8b stands for Cyano
  • X 2 , A, R 1 , R 2 , R 4 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the general meanings given above, as well as agrochemically active salts of these connections.
  • the compounds of the invention are generally defined by the formula (Ib).
  • X lb is nitrogen or CR 3b .
  • R 3b is hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OisoPr, OBu, OsecBu, OisoBu, OtertBu, OPentyl, O "eoPentyl O- (CH 2 ) 2 OH, O - (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OH, O- (CH 2 ) 3 OCH 3 , O -cylopentyl, O-cyclopropyl, O-cyclpbutyl, O-cyclohexyl, OCF 3 , OCF 2 H 1 OCFH 2 , OCF 2 CF 3 , OCF 2 CF 2 H OCH 2 CF 2 H , OCH 2 CF 3, OCH 2 CH 2 N (C 2 Hs) 2 , OCH 2 CH 2 N (CH 3 ) 2 , OCH ( CH 3 ) CH 2 OCH 3 , SH
  • R 8b stands for Cyano
  • X 2 , A, R 1 , R 2 , R 4 to R 7 , R 1 ⁇ , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the meanings given above, as well as agrochemically active salts of these connections.
  • X lb is nitrogen or CR 3b
  • R 3b is hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OisoP ⁇ , OBu, OsecBu, OisoBu, OtertBu, O- (CH 2 ) 2 OH, O- (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OH, O- (CH 2 ) 3 OCH 3 , O-cyclopentyl, OCF 3 , OCF 2 H, OCF 2 CF 3 , OCF 2 CF 2 H , OCH 2 CH 2 N (C 2 Hs) 2 , OCH (CH 3 ) CH 2 OCH 3, SH, SMe, SPh, SEt, SPr, SisoPr, SBu, SsecBu, SisoBu, StBu, SPentyl, SsecPentyl, SneoPentyl, SOctyl, S
  • R 8b stands for Cyano
  • X 2 , A, R 1 , R 2 , R 4 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the above-mentioned particularly preferred meanings, as well as agrochemically active salts of these connections.
  • X lb is nitrogen or CR 3b .
  • R 3b is hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OisoPr, OBu, OsecBu, O / so Bu, OtertBu, (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OCH 3 , O -cylopentyl, OCF 3 , OCF 2 H, OCF 2 CF 3 , OCF 2 CF 2 H OCH 2 CH 2 N (C 2 H 5 ) ; , OCH (CH 3 ) CH 2 OCH 3, SH, SMe, SPh, SEt, SPr, SisoP ⁇ , SBu, SsecBu, SisoBu, StBu, SPentyl, SsecPentyl, SrceoPentyl, SOctyl, SCF 3, SCF 2 H, SOMe, SO Et, SO-Pr, SOisoF ⁇ , SOBuBu, SOsecBu , SO
  • R 8b stands for Cyano
  • X 2 , A, R 1 , R 2 , R 4 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the above-mentioned very particularly preferred meanings, as well as agrochemically active Salts of these compounds.
  • X lb is nitrogen or CR 3b .
  • R 8b stands for Cyano
  • X 2 , A, R 1 , R 2 , R 4 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the above-mentioned particularly preferred meanings, as well as agrochemically active salts of these connections.
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt
  • R 11 is H
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • both R 1 ' are simultaneously methyl or fluorine.
  • X lb is nitrogen or CR 3b
  • X 2 is nitrogen or CR 4
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is CH 2 OPh
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is hydrogen, Me, CF 3 , OEt, COOH, COOMe, COOEt, phenyl, benzyl, 2-chlorophenyl, 3-fluorophenyl, 3-bromophenyl, 3-trifluoromethylphenyl, 3-chlorophenyl, 3-methoxyphenyl, 4-methoxyphenyl, CH 2 OPh,
  • R 11 is identical or different hydrogen, fluorine, methyl, CF 3 , phenyl, OEt, SMe, 4-fluorophenyl, 4-methylphenyl,
  • both R 11 are simultaneously methyl or fluorine.
  • X lb is CR 3b
  • X 2 is CR 4 ,
  • X lb is CR 3b
  • R 10 is H or Me
  • R 11 is H
  • X lb is CR 3b
  • X 2 is CR 4 ,
  • R 6 is H, CHO, COCH 3 , COCF 3 ,
  • R 7 is H
  • R 9 is H, Me, CHO, COCH 3 the remaining substituents having one or more of the meanings mentioned above,
  • R 1 is H
  • R 5 is H
  • R 1 is H
  • R 5 is H
  • X lb is CR 3b
  • X 2 is CR 4 ,
  • X lc is nitrogen or CR 3c ,
  • X 2c is nitrogen or CR 4c ,
  • R 2c and R 4c are independently hydrogen, halogen, cyano, hydroxy, nitro, a 3- to 8-membered, unsubstituted or substituted, saturated or unsaturated cycle containing no or up to four heteroatoms selected from N, O and S where two oxygen atoms are not adjacent, OMe, OEt, OPr, OisoPr, OBu, OsecBu, OisoBu, OtertBu, OPentyl, O ⁇ eoPentyl O- (CH 2 ) 2 OH, O- (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OH, O- (CH 2 ) 3 OCH 3 , O -cyclopentyl, O -cyclopropyl, O -cyclobutyl, O-cyclohexyl, OCF 3 , OCF 2 H, OCFH 2 , OCF 2 CF 3 , OCF 2 CF 2 H, OCH 2 CF 2 H, OCH 2
  • each two adjacent radicals R 2c , R 3c or R 4c optionally via R 12 or R 13 , together form a 3- to 7-membered, unsubstituted or substituted, saturated or unsaturated cycle, the no or may contain up to four heteroatoms selected from N, O and S, wherein two oxygen atoms are not adjacent;
  • R 3c is hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OisoPr, OBu, OsecBu, OisoBu, OtertBu, OPentyl, OweoPentyl O- (CH 2 ) 2 OH, O- ( CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OH, O- (CH 2 ) 3 OCH 3 , O -cylopentyl, O-cyclopropyl, O-cyclpbutyl, O-cyclohexyl, OCF 3 , OCF 2 H 3 OCFH 2 , OCF 2 CF 3 , OCF 2 CF 2 H, OCH 2 CF 2 H , OCH 2 CF 3, OCH 2 CH 2 N (C 2 H 5 ) ; , OCH 2 CH 2 N (CH 3 ) 2, OCH (CH 3 ) CH 2 OCH 3 , SH,
  • R 8c is fluorine
  • R 1 , R 5 to R 7 , R 1 ⁇ , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the general meanings given above, as well as agrochemically active salts of these compounds.
  • the compounds of the invention are generally defined by the formula (Ic).
  • X lc is nitrogen or CR 3c ,
  • X 2c is nitrogen or CR 4c ,
  • R 2c , R 40 and R 3c are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, O / soPr, OBu, OsecBu, OisoBu, OtertBu, O- (CH 2 ) 2 OH, 0- (CHZ) 2 OCH 3, O (CH 2) 3 OH, O- (CH 2) 3 OCH 3, O-cyclopentyl, OCF 3, OCF 2 H, OCF 2 CF 3, OCF 2 CF 2 H OCH 2 CH 2 N (C 2 Hj) 2 , OCH (CH 3 ) CH 2 OCH 3, SH, SMe, SPh, SEt, SPr, SisoFr, SBu, SsecBu, SisoBu, StBu, SPentyl, SsecPentyl, SneoPentyl, SOctyl, SCF 3 , SCF 2 H, SOMe, SO-Et, SO-
  • R 8c is fluorine
  • R 1 , R 5 to R 7 , R IA , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the preferred meanings given above, as well as agrochemically active salts of these compounds.
  • X lc is nitrogen or CR 3c ,
  • X 2c is nitrogen or CR 4c ,
  • R 2c , R 4c and R 3c are independently hydrogen, fluorine, chlorine, bromine, iodine,
  • R 8c is fluorine
  • R 1 , R 5 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the above-mentioned particularly preferred meanings, as well as agrochemically active salts of these compounds.
  • X lc is nitrogen or CR 3c ,
  • X 2c is nitrogen or CR 40 ,
  • R 2c , R 3c and R 4c are independently hydrogen, fluoro, chloro, bromo, iodo, cyano, hydroxy, nitro, OMe, OEt, OPr, OisoPr, OBu, OsecBu, O / so Bu, OtertBu, O- (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OCH 3 , O -cylopentyl, OCF 3 , OCF 2 H, OCF 2 CF 3, OCF 2 CF 2 H, OCH 2 CH 2 N (C 2 Hs) 2, OCH (CH 3 ) CH 2 OCH 3, SH, SMe, SPh, SEt, SPr, S / soPr, SBu, SsecBu, SisoBu, StBu, SPentyl, SsecPentyl, SneoPentyl, SOctyl, SCF 3 , SCF 2 H, SOMe, SO 2 Me, SO 2 CF 3 , SO
  • NHCOCH 2 OCH 3 NHCO (CH 2 ) 2 OCH 3 , N (C 2 H 5 ) COCH 3 , N (CH 3 ) COC (CH 3 ) 3 , N (C 2 H 5 ) COOCH 3 , NHCHO, N ( CH 3 ) CHO, NMe 2 , NEt 2 , NHMe, NH 2 , NRtertBu, NHEt, NHPr, NH / soPr, NHBu, NHwoBu, NHsecBu, cyclopropylamino, NHCH (CH 3 ) CH 2 OCH 3 , NCH 3 COCH 3 , acetyl (cyclopropyl) amino, [(1-methylcyclopropyl) carbonyl] amino, NHSO 2 CH 3 NHSOMe, NHSO 2 Me, NHSOCF 3 , NHSO 2 CF 3 , OCONHCH 3 , OCONHEt, OCONHPr, OCONH / soPr,
  • R 8c is fluorine
  • R 1 , R 5 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the above-mentioned very particularly preferred meanings, as well as agrochemically active salts of these compounds.
  • R 10 is H, OEt
  • R 11 is H
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • both R 1 ' are simultaneously methyl or fluorine.
  • X 2c is nitrogen or CR 4c
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is CH 2 OPh
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is hydrogen, Me, CF 3 , OEt, COOH, COOMe, COOEt, phenyl, benzyl, 2-chlorophenyl, 3-fluorophenyl, 3-bromophenyl, 3-trifluoromethylphenyl, 3-chlorophenyl, 3-methoxyphenyl, 4-methoxyphenyl, CH 2 OPh,
  • R 11 is identical or different hydrogen, fluorine, methyl, CF 3 , phenyl, OEt, SMe, 4-fluorophenyl, 4-methylphenyl, where only one R 10 or R 11 is not hydrogen,
  • both R 1 ' are simultaneously methyl or fluorine.
  • X lc is CR 3c
  • X 2c is CR 4c ,
  • X 2c is nitrogen
  • X lc is CR 3c
  • X 2c is nitrogen
  • R 11 is H
  • X lc is CR 3c
  • X 2c is CR 4c ,
  • R 6 is H, CHO, COCH 3 , COCF 3 ,
  • R 7 is H
  • R 9 is H, Me, CHO, COCH 3
  • R 1 is H
  • R 5 is H
  • R 1 is H
  • R 5 is H
  • X 1 is CR 3c and X 2c is CR 40 ,
  • R 1 to R 5 correspond to the abovementioned definitions, with the exception of the following cases: either X 1 is CR 3 and R 2 and R 3 form the following subunit of the general formula (Id):
  • X 1 is CR 3 and X 2 is CR 4 and R 4 and R 3 in the above subunit of general formula (Id) also form a (2-oxo-2,3-dihydro-1H-indol-5-yl ) amino; and
  • R 8d stands for CF 3
  • X 1 , X 2 , A, R 6 , R 7 R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the abovementioned general, preferred, particularly preferred, very particularly preferred and in particular preferred meanings, as well as agrochemically active salts of these compounds.
  • A is a direct bond, methylene or -CH (CH 3 ) - R 10 is H, OEt
  • R 11 is H
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • both R 1 ' are simultaneously methyl or fluorine.
  • X 1 is nitrogen or CR 3
  • X 2 is nitrogen or CR 4
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is CH 2 OPh
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is hydrogen, Me, CF 3 , OEt, COOH, COOMe, COOEt, phenyl, benzyl, 2-chlorophenyl, 3-fluorophenyl, 3-bromophenyl, 3-trifluoromethylphenyl, 3-chlorophenyl, 3-methoxyphenyl, 4-methoxyphenyl, CH 2 OPh,
  • R 11 is identical or different hydrogen, fluorine, methyl, CF 3 , phenyl, OEt, SMe, 4-fluorophenyl, 4-methylphenyl,
  • both R 1 ' are simultaneously methyl or fluorine.
  • X 1 is CR 3 and
  • X 2 is CR 4 ,
  • X 1 is nitrogen
  • X 1 is CR 3 and
  • R 10 is H or Me
  • R 11 is H
  • X 1 is CR 3 and
  • X 2 is CR 4 ,
  • R 6 is H, CHO, COCH 3 , COCF 3 ,
  • R 7 is H
  • R 9 is H, Me, CHO, COCH 3
  • R 1 is H
  • R 5 is H
  • R 1 is H
  • R 5 is H
  • X 1 is CR 3 and
  • X 2 is CR 4 , the remaining substituents having one or more of the meanings mentioned above,
  • X le is nitrogen or CR 3e ,
  • Y e e is hydrogen, halogen, cyano, hydroxy, nitro, a 3- to 8-membered, unsubstituted or substituted, saturated or unsaturated cycle which contain no or up to four hetero atoms selected from N, O and S , where two oxygen atoms are not adjacent, OR 12 , SR 12 , SOR 12 , SO 2 R 12 , SON (R 12 ) 2 , SO 2 NHMe, SO 2 NMe 2 , SO 2 NHAc, SO 2 NMeAc, SO 2 N (cyclopropyl) Ac, SO 2 NHPh, SO 2 NHbenzyl, SO 2 NHwBu, SO 2 NEt 2 , SO 2 NHEt, SO 2 NPr 2 , SO 2 NHPr, SO 2 NHcyclopropyl, SO 2 NHtertBu, SO 2 NHCF 3 , SO 2 N (CF 3 ) 2 , SO 2 NH (CH 2 ) 3 NMe 2 , SO
  • R 8e stands for Br
  • X 2 , A, R 1 , R 2 , R 4 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the general meanings given above, as well as agrochemically active Salts of these compounds.
  • X le is nitrogen or CR 3e ,
  • R 3e is hydrogen, fluoro, chloro, bromo, iodo, cyano, hydroxy, nitro, OMe, OEt, OPr, OisoP ⁇ , OBu, OsecBu, O / so Bu, OtertBu, OPentyl, OneoPentyl O- (CH 2 ) 2 OH, O - (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OH, O- (CH 2 ) 3 OCH 3 , O -cylopentyl, O-cyclopropyl, O-cyclpbutyl, O-cyclohexyl, OCF 3 , OCF 2 H , OCFH 2 , OCF 2 CF 3 , OCF 2 CF 2 H, OCH 2 CF 2 H , OCH 2 CF 3, OCH 2 CH 2 N (C 2 H 5 ) 2 , OCH 2 CH 2 N (CH 3 ) 2, OCH (CH 3 ) CH 2 OCH 3
  • R 8e stands for Br
  • X le is nitrogen or CR 3e ,
  • R 3e is hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OisoP ⁇ , OBu, OsecBu, OwoBu, OtertBu, O- (CH 2 ) 2 OH, O- (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OH, O- (CH 2 ) 3 OCH 3 , O-cyclopentyl, OCF 3 , OCF 2 H, OCF 2 CF 3, OCF 2 CF 2 H , OCH 2 CH 2 N (C 2 Hj) 2, OCH (CH 3 ) CH 2 OCH 3, SH, SMe, SPh, SEt, SPr, SisoP ⁇ , SBu, SsecBu, SwoBu, SiBu, SPentyl, SsecPentyl, SneoPentyl, SOctyl, SCF 3 , SCF 2 H, SOMe, SO-Et, SO
  • R 8e stands for Br
  • X 2 , A, R 1 , R 2 , R 4 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the above-mentioned particularly preferred meanings, as well as agrochemically active salts of these connections.
  • X le is nitrogen or CR 3e ,
  • R 3e is hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OisoPr, OBu, OsecBu, OisoBu, OtertBu, (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OCH 3 , O-cyclopentyl, OCF 3 , OCF 2 H, OCF 2 CF 3 , OCF 2 CF 2 H, OCH 2 CH 2 N (C 2 Hs) 2, OCH (CH 3 ) CH 2 OCH 3 , SH, SMe , SPh, SEt, SPr, SwoPr, SBu, SsecBu, SisoBu, SfBu, SPentyl, SsecPentyl, SweoPentyl, SOctyl, SCF 3 , SCF 2 H, SOMe, SO-Et, SO-Pr, SO-woPr, SOBuBu, SOsecBu, SO
  • NHCO (CH 2 ) 2 OCH 3 NHCO (CH 2 ) 3 OCH 3 , N (CH 3 ) COCH 3 , N (C 2 H 5 ) COCH 3 , N (CH 3 ) COC (CH 3 ) 3 , N ( C 2 H 5 ) COOCH 3 , NHCHO, N (CH 3 ) CHO, NMe 2 , NEt 2 , NHMe, NH 2 , NHtertBu, NHEt, NHPr, NHwoPr, NHBu, NHwoBu, NHsecBu, cyclopropylamino, NHCH (CH 3 ) CH 2 OCH 3, NCH 3 COCH 3 , acetyl (cyclopropyl) amino, [(1-methylcyclopropoxycarbonyloxy), piperazin-1-yl, 4
  • R 8e stands for Br
  • X 2 , A, R 1 , R 2 , R 4 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the above-mentioned very particularly preferred meanings, as well as agrochemically active Salts of these compounds.
  • X le is nitrogen or CR 3e ,
  • R 3e is hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OisoPr, OBu, OsecBu, OisoBu, OtertBu, O- (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OCH 3 , O -cylopentyl, OCF 3 , OCF 2 H, OCF 2 CF 3, OCF 2 CF 2 H OCH 2 CH 2 N (C 2 H 5 ) ; , OCH (CH 3 ) CH 2 OCH 3, SH, SMe, SPh, SEt, SPr, SwoPr, SBu, SsecBu, S / soBu, SfBu, SPentyl, SsecPentyl, S ⁇ eoPentyl, SOctyl, SCF 3 , SCF 2 H, SOMe, SO 2 Me, SO 2 CF 3 , SO 2 Et, SO 2 Pr, SO 2 CH
  • R 8e stands for Br
  • X 2 , A, R 1 , R 2 , R 4 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the above-mentioned particularly preferred meanings, as well as agrochemically active salts of these connections.
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt
  • R 11 is H
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me the remaining substituents having one or more of the meanings mentioned above,
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • both R 1 ' are simultaneously methyl or fluorine.
  • X le is nitrogen or CR 3e
  • X 2 is nitrogen or CR 4
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is CH 2 OPh
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is hydrogen, Me, CF 3 , OEt, COOH, COOMe, COOEt, phenyl, benzyl, 2-chlorophenyl, 3-fluorophenyl, 3-bromophenyl, 3-trifluoromethylphenyl, 3-chlorophenyl, 3-methoxyphenyl, 4-methoxyphenyl, CH 2 OPh,
  • R 11 is identical or different hydrogen, fluorine, methyl, CF 3 , phenyl, OEt, SMe, 4-fluorophenyl, 4-methylphenyl,
  • both R 1 ' are simultaneously methyl or fluorine.
  • X le is CR 3e and
  • X 2 is CR 4 ,
  • X le is CR 3e and
  • R 10 is H or Me
  • R 11 is H
  • X le is CR 3e and
  • X 2 is CR 4 ,
  • R 6 is H, CHO, COCH 3 , COCF 3 ,
  • R 7 is H
  • R 9 is H, Me, CHO, COCH 3
  • R 1 is H
  • R 5 is H
  • R 1 is H
  • R 5 is H
  • X le is CR 3e and
  • X 2 is CR 4 ,
  • each two adjacent radicals R 2 , R 3 or R 4 can together form a 3 to 7-membered, unsubstituted or substituted, saturated or unsaturated cycle, the no or bis may contain four heteroatoms selected from N, O and S, wherein two oxygen atoms are not adjacent; and
  • R 8f is methyl
  • X 1 , X 2 , A, R 2 , R 3 , R 4 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the general meanings given above, as well as agrochemical effective salts of these compounds.
  • R lf is hydrogen, fluorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OisoPr, OBu, OsecBu, OisoBu, OtertBu, OPentyl, OneoPentyl O- (CH 2 ) 2 OH, O- (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OH, O- (CH 2 ) 3 OCH 3 , O -cylopentyl, O-cyclopropyl, O-cyclpbutyl, O-cyclohexyl, OCF 3 , OCF 2 H, OCFH 2 , OCF 2 CF 3 , OCF 2 CF 2 H, OCH 2 CF 2 H, OCH 2 CF 3, OCH 2 CH 2 N (C 2 Hs) 2 , OCH 2 CH 2 N (CH 3 ) 2, OCH (CH 3 ) CH 2 OCH 3 , SH, SMe, SP
  • R 8f is methyl and X 1 , X 2 , A, R 2 , R 3 , R 4 to R 7 , R l A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the preferred meanings given above, as well as agrochemical effective salts of these compounds.
  • R lf is hydrogen, fluorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OwoPr, OBu, OsecBu, OisoBu, OtertBu, O- (CH 2 ) 2 OH, O- (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OH, O- (CH 2 ) 3 OCH 3 , O-cyclopentyl, OCF 3 , OCF 2 H, OCF 2 CF 3, OCF 2 CF 2 H , OCH 2 CH 2 N (C 2 H 5 ) ; , OCH (CH 3 ) CH 2 OCH 3, SH, SMe, SPh, SEt, SPr, SwoPr, SBu, SsecBu, SwoBu, SrBu, SPentyl, SsecPentyl, S ⁇ eoPentyl, SOctyl, SCF 3 , SCF 2 H, SOMe, SO-E
  • R 8f is methyl
  • X 1 , X 2 , A, R 2 , R 3 , R 4 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the above-mentioned particularly preferred meanings, and agrochemically active salts of these compounds.
  • R lf is hydrogen, fluorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OwoPr, OBu, OsecBu, OisoBu, OtertBu, (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OCH 3 , O-cyclopentyl, OCF 3 , OCF 2 H, OCF 2 CF 3 , OCF 2 CF 2 H , OCH 2 CH 2 N (C 2 H 5 ) ; , OCH (CH 3 ) CH 2 OCH 3, SH, SMe , SPh, SEt, SPr, SisoPr, SBu, SsecBu, SisoBu, StBu, SPentyl, SsecPentyl, S / ioPentyl, SOctyl, SCF 3 , SCF 2 H, SOMe, SO-Et, SO-Pr, SOwoPr, SOBuBu, SO
  • NHCOC (CH 3 ) 2 CH 2 Cl, NHCO (C CH 2 ) CH 3, NHCON (CH 3 ) 2 , NHCOCH 2 OCH 3 , NHCO (CH 2 ) 2 OCH 3 , NHCO (CH 2 ) 3 OCH 3 , N (CH 3 ) COCH 3 , N (C 2 H 5 ) COCH 3 , N (CH 3 ) COC (CH 3 ) 3 , N (C 2 H 5 ) COOCH 3 , NHCHO, N (CH 3 ) CHO, NMe 2 , NEt 2 , NHMe, NH 2 , NHtertBu, NHEt, NHPr, NHwoPr, NHBu, NHwoBu, NHsecBu, cyclopropylamino, NHCH (CH 3 ) CH 2 OCH 3, NCH 3 COCH 3 , acetyl (cyclopropyl) amino, [(1 -methylcyclopropyl) carbon
  • R 8f is methyl
  • X 1 , X 2 , A, R 2 to R 7 , R 1 A , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the above-mentioned very particularly preferred meanings, as well as agrochemically active salts of these compounds ,
  • R lf is hydrogen, fluorine, bromine, iodine, cyano, hydroxy, nitro, OMe, OEt, OPr, OisoP ⁇ , OBu, OsecBu, O / so Bu, OtertBu, O- (CH 2 ) 2 OCH 3 , O- (CH 2 ) 3 OCH 3 , O -cylopentyl, OCF 3 , OCF 2 H, OCF 2 CF 3, OCF 2 CF 2 H OCH 2 CH 2 N (C 2 H 5 ) 2, OCH (CH 3 ) CH 2 OCH 3, SH , SMe, SPh, SEt, LAn, SisoPr, SBu, SsecBu, SisoBu, StBu, SPentyl, SsecPentyl, S " ⁇ ?
  • R 8f is methyl
  • X 2 , A, R 2 , R 3 , R 4 to R 7 , R NA , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the above-mentioned particularly preferred meanings, as well as agrochemically active salts thereof Links.
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me the remaining substituents having one or more of the meanings mentioned above,
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is H, OEt, CO 2 Et, 2-Cl-phenyl, phenyl, CH 2 OPh
  • R 11 is H, F, Cl, Me
  • both R 11 are simultaneously methyl or fluorine.
  • X 1 is nitrogen or CR 3
  • X 2 is nitrogen or CR 4
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is CH 2 OPh
  • A is a direct bond, methylene or -CH (CH 3 ) -
  • R 10 is hydrogen, Me, CF 3 , OEt, COOH, COOMe, COOEt, phenyl, benzyl, 2-chlorophenyl, 3-fluorophenyl, 3-bromophenyl, 3-trifluoromethylphenyl, 3-chlorophenyl, 3-methoxyphenyl, 4-methoxyphenyl, CH 2 OPh,
  • R 11 is identical or different hydrogen, fluorine, methyl, CF 3 , phenyl, OEt, SMe, 4-fluorophenyl, 4-methylphenyl,
  • both R 1 ' are simultaneously methyl or fluorine.
  • X 1 is CR 3 and
  • X 2 is CR 4 ,
  • X 1 is nitrogen
  • X 1 is CR 3 and
  • R 10 is H or Me
  • R 11 is H
  • X 1 is CR 3 and
  • X 2 is CR 4 ,
  • R 6 is H, CHO, COCH 3 , COCF 3 ,
  • R 7 is H
  • R 9 is H, Me, CHO, COCH 3
  • R lf is H
  • R 5 is H
  • R lf is H
  • R 5 is H
  • X 1 is CR 3 and
  • X 2 is CR 4 ,
  • the compounds of the formula (Ia), (Ib), (Ic), (Id), (Ie) and (If) can be used both in pure form and as mixtures of various possible isomeric forms, in particular of stereoisomers, such as E and Z. -, threo and erythro, as well as optical isomers, such as R and S isomers or atropisomers, but optionally also of tautomers. Both the E and the Z isomers, as well as the threo and erythro, and the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms claimed.
  • stereoisomers such as E and Z. -, threo and erythro
  • optical isomers such as R and S isomers or atropisomers
  • the compounds of the formulas (I), (Ia), (Ib), (Ic), (Id), (Ie) and (If) have acidic or basic properties and can with inorganic or basic form organic acids or with bases or with metal ions salts, optionally also internal salts or adducts. If the compounds of the formulas (I), (Ia), (Ib), (Ic), (Id), (Ie) and (If) bear amino, alkylamino or other basic-property-inducing groups, these compounds can be added with acids Salts are reacted or fall through the synthesis directly as salts.
  • inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid and acid salts such as NaHSO 4 and KHSO 4 .
  • Suitable organic acids are, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms ), Arylsulfonic acids or -disulfonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or -diphosphonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two phosphonic acid radical
  • the salts thus obtainable also have fungicidal properties.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 8 carbon atoms, for example C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1,1-dimethylethyl, Pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2- Ethy
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 8 carbon atoms and a double bond in any position, for example C 2 -C ö alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, IButenyl, 2-butenyl, 3Butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 - Methyl IButenyl, 2-Methyl-IButenyl, 3-Methyl-1-Butenyl, 1-Methyl-2Butenyl, 2-Methyl-2Butenyl, 3-Methyl-2Butenyl, 1-Methyl-3-Butenyl, 2-Methyl-3-Butenyl, 3-Methy
  • Alkynyl straight-chain or branched hydrocarbon groups having 2 to 8 carbon atoms and a triple bond in any position, for example C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, IButinyl, 2-butyl, 3-butyl, 1-methyl-2 propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2 propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentyny
  • Cylcoalkenyl monocyclic, non-aromatic hydrocarbon groups having 3 to 8 carbon ring members having at least one double bond, such as cyclopenten-1-yl, cyclohexene-1-yl, cyclohepta-1,3-dien-1-yl;
  • Alkoxycarbonyl an alkoxy group having 1 to 6 carbon atoms (as mentioned above), which is bonded to the skeleton via a carbonyl group (-CO-);
  • Oxyalkylene oxide divalent unbranched chains of 1 to 3 CH 2 groups, both valences being bonded to the skeleton via an oxygen atom, eg OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O;
  • heterocyclyl mono- or bicyclic heterocycles (heterocyclyl) containing in addition to carbon ring members one to three nitrogen atoms and / or an oxygen or sulfur atom or a or two oxygen and / or sulfur atoms; if the ring contains several oxygen atoms, these are not directly adjacent; eg oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5 Isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl
  • Hexahydropyrimidinyl 5-hexahydropyrimidinyl, 2-piperazinyl, 1, 3,5-hexahydro-triazin-2-yl, and 1, 2,4-hexahydrotriazin-3-yl;
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom 5-membered heteroaryl groups which may contain, besides carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members , eg 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3 Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2,4-oxadiazole 3-yl, 1,2,4-ox
  • 5-membered heteroaryl groups containing, besides carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms, respectively May contain ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-l, 3-diene-l, 4-diyl group in which one or two carbon atoms replaced by N atoms may be replaced in which one or two carbon atoms by N atoms, these rings are bonded via one of the nitrogen ring members to the skeleton, eg 1-pyrrolyl, 1-pyrazolyl, 1,2,4-triazol-1-yl, 1-imidazolyl, 1,2,3-triazol-1-yl, 1,3,4-triazol-1-yl;
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-membered ring heteroaryl groups which, in addition to carbon atoms, have one to three or one to four nitrogen atoms may contain as ring members, for example 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, l, 3,5-triazin-2-yl and l, 2,4-triazine 3-yl;
  • a further subject matter of the present invention relates to a process for preparing the diaminopyrimidines according to the invention of the formulas (Ia), (Ib), (Ic), (Id), (Ie) and (If) comprising at least one of the following steps (a) to ( e):
  • a suitable base at a temperature of -30 0 C to +80 0 C in a suitable solvent such as dioxane, THF, dimethylformamide or acetonitrile, a cyclopropylamine (H) with a 2,4-dihalopyrimidine (III) via a Period of 1-24 h reacted.
  • a suitable solvent such as dioxane, THF, dimethylformamide or acetonitrile
  • the base for example, inorganic salts such as NaHCO 3 , Na 2 CO 3 or K 2 CO 3 , organometallic compounds such as LDA or NaHMDS or amine bases such as ethyldiisopropylamine, DBU, DBN or tri-n-butylamine can be used.
  • reaction may also be carried out as described, for example, in Org. Lett. 2006, 8, 395, with the aid of a suitable transition metal catalyst, for example palladium, together with a suitable ligand, for example triphenylphosphine or xanthphos.
  • a suitable transition metal catalyst for example palladium
  • a suitable ligand for example triphenylphosphine or xanthphos.
  • R 7 , R 8d , R 9 , R 10 , R 11 and R 14 have the abovementioned general, preferred, particularly preferred and very particularly preferred meanings as defined above.
  • R 8a is chlorine, iodine, CFH 2 , CF 2 H or CCl 3
  • R 8a and Y are chlorine and A is a direct bond
  • R 10 can not be equal to CO 2 H or CO 2 Me
  • R 8b represents cyano with the proviso that when Y is chlorine and A is a direct bond, R 10 and R 11 may not be hydrogen at the same time
  • R 8c is fluorine with the proviso that when Y is chlorine and A is a direct bond, R 10 and R 11 may not be hydrogen at the same time
  • R 8e stands for Br
  • R 10 and R 11 may not be hydrogen at the same time
  • R 8f is methyl with the proviso that when Y is chloro and A is methylene or a direct bond, R 9 can not be nPr.
  • One way to represent compound (Ia), (Ib), (Ic), (Id), (Ie) and (If) is shown in Scheme 2.
  • the substituted aromatic amines are either commercially available or can be prepared by methods known from the literature from commercially available precursors.
  • Aromatic amines bearing one or more of the same or different substituents in the aromatic moiety can be prepared by a variety of methods described in the pertinent literature. Below are examples of some of the methods mentioned.
  • sulfonamide- or sulfonic acid-substituted arylamines succeeds, for example, by reaction of commercially available aminosulphonic acids known from the literature with chlorinating reagents (for example POCl 3 ) and subsequent reaction of the sulfochlorides formed with O- or N-nucleophiles.
  • chlorinating reagents for example POCl 3
  • N-monoacylated diaminoaromatics Two common methods for preparing N-monoacylated diaminoaromatics are outlined below.
  • nitroanilines can be reacted by standard methods with acyl halides, chloroformates or iso (thio) cyanates to give the corresponding N-acyl nitroaromatics, which can then be reduced to N-acyl amino aromatics by literature procedures.
  • Another method describes the preparation of the compounds mentioned by means of transition-metal-catalyzed cross-coupling of aminohaloaromatics and N-acyl compounds (see, for example, J. Am. Chem. Soc., 2001, 123, 7727).
  • Cyclic, N-bonded radicals R 1 to R 5 can be prepared, for example, by condensation of nitroaminoaromatics with haloalkylcarbonyl halides or diesters or diester equivalents or lactones; the subsequent reduction of the nitro group provides the desired aromatic amine.
  • Another possibility for the synthesis of N-linked radicals R 1 to R 5 is the condensation of nitroarylhydrazines with diesters or diester equivalents, propargyl acid esters or keto esters. Reduction of the nitro group gives the aniline.
  • the intermediate (V) is in the presence of Bronsted acids such as anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid in a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile at a temperature of 0 0 C-140 0 C over a period of 1-48 h with an aromatic amine (TV) reacted.
  • Bronsted acids such as anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid in a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile
  • a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile
  • reaction of (V) and (IV) to (Ia), (Ib), (Ic), (Id), (Ie) and (If) also base catalysis ie using, for example, carbonates such as potassium carbonate, alcoholates such Potassium tert-butylate or hydrides such as sodium hydride can be carried out, while also the catalytic use of a transition metal such as palladium may be useful together with a suitable ligands such as xanthophos.
  • reaction of (VIb) and (TV) to (IX) can also be base catalysed, that is, carried out using, for example, carbonates such as potassium carbonate, alcoholates such as potassium tert-butylate or hydrides such as sodium hydride, including the catalytic use of a transition metal for example, palladium may be useful together with a suitable ligand such as xanthphos.
  • X 1 , X 2 , R 1 to R 5 , R 8d " e , R 12 and R 13 have the abovementioned general, preferred, particularly preferred, very particularly preferred and especially preferred meanings,
  • R 6 and R 7 is hydrogen.
  • R 8a is chlorine, iodine, CFH 2 , CF 2 H, CCl 3 with the proviso that if
  • R 3 may not be H, CO 2 H, (CH 2 ) 2 OH, SMe, SOMe, SO 2 NH 2 or cyano
  • neither R 2 nor R 4 may be OH or CONH 2 .
  • Intermediates of formula (IX) can be prepared by reaction with suitable halogenating agents such as thionyl chloride, phosphorus pentoxide or phosphoryl chloride or a mixture thereof, optionally in the presence of a suitable solvent such as toluene or ethanol and optionally in the presence of a suitable base such as triethylamine Convert 2-anilino-4-chlo ⁇ yrimidines of the formula (X).
  • suitable halogenating agents such as thionyl chloride, phosphorus pentoxide or phosphoryl chloride or a mixture thereof
  • a suitable solvent such as toluene or ethanol
  • a suitable base such as triethylamine
  • X 1 , X 2 , R 2 to R 4 , R 7 , R 8d , R 8e , R 12 and R 13 have the abovementioned general, preferred, particularly preferred, very particularly preferred and especially preferred meanings and
  • Hal is fluorine, chlorine, bromine or iodine
  • R 8a is chlorine, iodine, CFH 2 , CF 2 H, CCl 3 and cyano
  • R 1 , R 5 and R 6 is hydrogen
  • R 3 is not identical to CON (Me) -4- (N-methylpiperidinyl), N-piperazinyl, CO-1- (4-methylpiperazinyl), N-morpholinyl, SO 2 Me, CONH 2 , Me, OMe, COO-benzyl, COOH, COCl, CN, SO 2 NH 2 , NO 2 , NMe 2 or Cl,
  • R 2 or R 4 is not CN, Cl or 5-oxazolyl
  • R 2 , R 3 and R 4 are not chlorine.
  • X 1 CR 3
  • X 2 CR 4
  • R 8d CF 3
  • R 2 and R 3 or R 3 and R 4 do not together form a saturated or partially unsaturated heterocycle
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Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009103652A1 (en) * 2008-02-22 2009-08-27 F. Hoffmann-La Roche Ag Modulators for amyloid beta
WO2009158571A1 (en) * 2008-06-27 2009-12-30 Avila Therapeutics And Uses Thereof Heteroaryl compounds and uses thereof
WO2010025831A1 (de) * 2008-09-03 2010-03-11 Bayer Cropscience Ag Heterozyklisch substituierte anilinopyrimidine als fungizide
WO2010028179A1 (en) * 2008-09-03 2010-03-11 Dr. Reddy's Laboratories Ltd. Heterocyclic compounds as gata modulators
WO2010025850A1 (de) * 2008-09-03 2010-03-11 Bayer Cropscience Ag Heterozyklisch substituierte anilinopyrimidine als fungizide
WO2010025833A1 (de) * 2008-09-03 2010-03-11 Bayer Cropscience Ag Alkoxy- und alkylthio-substituierte anilinopyrimidine
WO2010025863A2 (de) * 2008-09-03 2010-03-11 Bayer Cropscience Ag 4-alkyl-substituierte diaminopyrimidine
EP2179992A1 (de) * 2008-10-21 2010-04-28 Bayer Schering Pharma Aktiengesellschaft Sulfonsubstituierte Anlinopyrimidinderivative als CDK-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel
WO2010135070A1 (en) * 2009-05-19 2010-11-25 Dow Agrosciences Llc Compounds and methods for controlling fungi
US7923450B2 (en) 2008-01-11 2011-04-12 Hoffmann-La Roche Inc. Modulators for amyloid beta
EP2468882A1 (de) 2010-12-27 2012-06-27 Bayer CropScience AG Aurorakinaseaktivatorpolypeptide zum Identifizieren von fungizid wirksamen Verbindungen
US8288403B2 (en) 2008-11-10 2012-10-16 Hoffmann-La Roche Inc. Heterocyclic gamma secretase modulators
US8338439B2 (en) 2008-06-27 2012-12-25 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidines useful as kinase inhibitors
US8354420B2 (en) 2010-06-04 2013-01-15 Genentech, Inc. Aminopyrimidine derivatives as LRRK2 inhibitors
US8389717B2 (en) 2008-10-09 2013-03-05 Hoffmann-La Roche Inc. Modulators for amyloid beta
US20130157999A1 (en) * 2011-11-29 2013-06-20 Genentech, Inc. Aminopyrimidine derivatives as lrrk2 modulators
US8486967B2 (en) 2010-02-17 2013-07-16 Hoffmann-La Roche Inc. Heteroaryl substituted piperidines
US8563568B2 (en) 2010-08-10 2013-10-22 Celgene Avilomics Research, Inc. Besylate salt of a BTK inhibitor
US8796255B2 (en) 2010-11-10 2014-08-05 Celgene Avilomics Research, Inc Mutant-selective EGFR inhibitors and uses thereof
US8815882B2 (en) 2010-11-10 2014-08-26 Genentech, Inc. Pyrazole aminopyrimidine derivatives as LRRK2 modulators
US8975249B2 (en) 2010-11-01 2015-03-10 Celgene Avilomics Research, Inc. Heterocyclic compounds and uses thereof
US9056839B2 (en) 2012-03-15 2015-06-16 Celgene Avilomics Research, Inc. Solid forms of an epidermal growth factor receptor kinase inhibitor
US9108927B2 (en) 2012-03-15 2015-08-18 Celgene Avilomics Research, Inc. Salts of an epidermal growth factor receptor kinase inhibitor
US9126950B2 (en) 2012-12-21 2015-09-08 Celgene Avilomics Research, Inc. Heteroaryl compounds and uses thereof
US9145387B2 (en) 2013-02-08 2015-09-29 Celgene Avilomics Research, Inc. ERK inhibitors and uses thereof
US9238629B2 (en) 2010-11-01 2016-01-19 Celgene Avilomics Research, Inc. Heteroaryl compounds and uses thereof
US9364476B2 (en) 2011-10-28 2016-06-14 Celgene Avilomics Research, Inc. Methods of treating a Bruton's Tyrosine Kinase disease or disorder
US9415049B2 (en) 2013-12-20 2016-08-16 Celgene Avilomics Research, Inc. Heteroaryl compounds and uses thereof
US9492471B2 (en) 2013-08-27 2016-11-15 Celgene Avilomics Research, Inc. Methods of treating a disease or disorder associated with Bruton'S Tyrosine Kinase
US9556126B2 (en) 2013-12-20 2017-01-31 Signal Pharmaceuticals, Llc Substituted diaminopyrimidyl compounds, compositions thereof, and methods of treatment therewith
US9908884B2 (en) 2009-05-05 2018-03-06 Dana-Farber Cancer Institute, Inc. EGFR inhibitors and methods of treating disorders
US10005760B2 (en) 2014-08-13 2018-06-26 Celgene Car Llc Forms and compositions of an ERK inhibitor
US11351168B1 (en) 2008-06-27 2022-06-07 Celgene Car Llc 2,4-disubstituted pyrimidines useful as kinase inhibitors

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK2300013T3 (en) 2008-05-21 2017-12-04 Ariad Pharma Inc PHOSPHORUS DERIVATIVES AS KINASE INHIBITORS
US9273077B2 (en) 2008-05-21 2016-03-01 Ariad Pharmaceuticals, Inc. Phosphorus derivatives as kinase inhibitors
AR077999A1 (es) 2009-09-02 2011-10-05 Vifor Int Ag Antagonistas de pirimidin y triazin-hepcidina
AU2012250517B2 (en) 2011-05-04 2016-05-19 Takeda Pharmaceutical Company Limited Compounds for inhibiting cell proliferation in EGFR-driven cancers
RS58475B1 (sr) * 2011-10-20 2019-04-30 Oryzon Genomics Sa Jedinjenja (hetero)aril ciklopropilamina kao lsd1 inhibitori
ES2638595T3 (es) * 2011-11-29 2017-10-23 Genentech, Inc. Derivados de aminopirimidina como moduladores de LRRK2
CA2850594C (en) * 2011-11-29 2020-03-10 F. Hoffmann-La Roche Ag Aminopyrimidine derivatives as lrrk2 modulators
CN104169272A (zh) * 2011-12-23 2014-11-26 赛尔佐姆有限公司 作为激酶抑制剂的嘧啶-2,4-二胺衍生物
EP2612554A1 (en) * 2012-01-09 2013-07-10 Bayer CropScience AG Fungicide compositions comprising fluopyram, at least one succinate dehydrogenase (SDH) inhibitor and optionally at least one triazole fungicide
AU2013204563B2 (en) 2012-05-05 2016-05-19 Takeda Pharmaceutical Company Limited Compounds for inhibiting cell proliferation in EGFR-driven cancers
US9611283B1 (en) 2013-04-10 2017-04-04 Ariad Pharmaceuticals, Inc. Methods for inhibiting cell proliferation in ALK-driven cancers
EP3144292B1 (en) * 2014-04-14 2020-08-26 Shanghai Haiyan Pharmaceutical Technology Co., Ltd 2,3,4,6-tetra-substituted benzene-1,5-diamine derivatives, preparation method therefor and medicinal use thereof
US10266549B2 (en) 2014-08-25 2019-04-23 Salk Institute For Biological Studies ULK1 inhibitors and methods using same
US10710983B2 (en) * 2016-06-27 2020-07-14 Rigel Pharmaceuticals, Inc. 2,4-diamino-pyrimidine compounds and method for making and using the compounds
WO2018069842A1 (en) * 2016-10-14 2018-04-19 Pi Industries Ltd 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms
CN109206373B (zh) * 2017-07-07 2022-02-15 上海医药工业研究院 一种帕博昔布中间体5-溴-2-氯-4-环戊基氨基嘧啶的制备工艺

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4029650A1 (de) * 1990-09-19 1992-03-26 Hoechst Ag 2-anilino-pyrimidine, verfahren zu ihrer herstellung, sie enthaltene mittel und ihre verwendung als fungizide
WO2002004429A1 (en) * 2000-07-11 2002-01-17 Astrazeneca Ab Pyrimidine derivatives
WO2002096888A1 (de) * 2001-05-29 2002-12-05 Schering Aktiengesellschaft Cdk inhibitorische pyrimidine, deren herstellung und verwendung als arzneimittel
WO2007140957A1 (de) * 2006-06-08 2007-12-13 Bayer Schering Pharma Aktiengesellschaft Sulfimide als proteinkinaseinhibitoren

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1581441A (en) 1976-01-29 1980-12-17 Dobson Park Ind Fluid powered impact tools
US4272417A (en) * 1979-05-22 1981-06-09 Cargill, Incorporated Stable protective seed coating
US4245432A (en) * 1979-07-25 1981-01-20 Eastman Kodak Company Seed coatings
US4808430A (en) * 1987-02-27 1989-02-28 Yazaki Corporation Method of applying gel coating to plant seeds
GB9510459D0 (en) 1995-05-24 1995-07-19 Zeneca Ltd Bicyclic amines
US5876739A (en) * 1996-06-13 1999-03-02 Novartis Ag Insecticidal seed coating
GB9624611D0 (en) 1996-11-26 1997-01-15 Zeneca Ltd Bicyclic amine compounds
US6503904B2 (en) * 1998-11-16 2003-01-07 Syngenta Crop Protection, Inc. Pesticidal composition for seed treatment
JP3533134B2 (ja) * 1999-02-15 2004-05-31 三井化学株式会社 フッ素化剤及びその製法と使用
RU15525U1 (ru) 2000-07-04 2000-10-20 Федеральный научно-производственный центр закрытое акционерное общество "Научно-производственный концерн (объединение) "ЭНЕРГИЯ" Электродвигатель постоянного тока
US6656317B2 (en) * 2001-09-28 2003-12-02 Reliance Electric Technologies, Llc Method for insulating electrical windings
JP2005526765A (ja) 2002-03-11 2005-09-08 シエーリング アクチエンゲゼルシャフト Ｃｄｋ−阻害性２−ヘテロアリール−ピリミジン類、それらの生成及び医薬としての使用
UA80767C2 (en) 2002-12-20 2007-10-25 Pfizer Prod Inc Pyrimidine derivatives for the treatment of abnormal cell growth
ES2338545T3 (es) 2002-12-20 2010-05-10 Pfizer Products Inc. Derivados de pirimidina para el tratamiento del crecimiento celular anormal.
KR101201603B1 (ko) 2003-07-30 2012-11-14 리겔 파마슈티칼스, 인크. 자가면역 질환의 치료 또는 예방에 사용하기 위한2,4-피리미딘디아민 화합물
EP1663242B1 (en) 2003-08-07 2011-04-27 Rigel Pharmaceuticals, Inc. 2,4-pyrimidinediamine compounds and uses as anti-proliferative agents
PL1663991T3 (pl) 2003-09-05 2007-04-30 Pfizer Prod Inc Selektywna synteza CF3 – podstawionych pirymidyn
BRPI0508230A (pt) 2004-03-30 2007-07-17 Chiron Corp derivados de tiofeno substituìdo como agentes anti-cáncer
US7521457B2 (en) 2004-08-20 2009-04-21 Boehringer Ingelheim International Gmbh Pyrimidines as PLK inhibitors

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4029650A1 (de) * 1990-09-19 1992-03-26 Hoechst Ag 2-anilino-pyrimidine, verfahren zu ihrer herstellung, sie enthaltene mittel und ihre verwendung als fungizide
WO2002004429A1 (en) * 2000-07-11 2002-01-17 Astrazeneca Ab Pyrimidine derivatives
WO2002096888A1 (de) * 2001-05-29 2002-12-05 Schering Aktiengesellschaft Cdk inhibitorische pyrimidine, deren herstellung und verwendung als arzneimittel
WO2007140957A1 (de) * 2006-06-08 2007-12-13 Bayer Schering Pharma Aktiengesellschaft Sulfimide als proteinkinaseinhibitoren

Cited By (80)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7923450B2 (en) 2008-01-11 2011-04-12 Hoffmann-La Roche Inc. Modulators for amyloid beta
WO2009103652A1 (en) * 2008-02-22 2009-08-27 F. Hoffmann-La Roche Ag Modulators for amyloid beta
US8962834B2 (en) 2008-02-22 2015-02-24 Hoffmann-La Roche Inc. Modulators of amyloid beta
US9212181B2 (en) 2008-06-27 2015-12-15 Celgene Avilomics Research, Inc. Substituted 2,4-diaminopyrimidines as kinase inhibitors
US8710222B2 (en) 2008-06-27 2014-04-29 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidines useful as kinase inhibitors
AU2009262068B2 (en) * 2008-06-27 2014-12-11 Celgene Car Llc Heteroaryl compounds and uses thereof
AU2009262068C1 (en) * 2008-06-27 2015-07-02 Celgene Car Llc Heteroaryl compounds and uses thereof
US10828300B2 (en) 2008-06-27 2020-11-10 Celgene Car Llc Substituted 2,4-diaminopyrimidines as kinase inhibitors
WO2009158571A1 (en) * 2008-06-27 2009-12-30 Avila Therapeutics And Uses Thereof Heteroaryl compounds and uses thereof
US9296737B2 (en) 2008-06-27 2016-03-29 Celgene Avilomics Research, Inc. Substituted 2,4-diaminopyrimidines as kinase inhibitors
US11351168B1 (en) 2008-06-27 2022-06-07 Celgene Car Llc 2,4-disubstituted pyrimidines useful as kinase inhibitors
US8609679B2 (en) 2008-06-27 2013-12-17 Celgene Avilomics Research, Inc. 2,4-diaminopyrimidines useful as kinase inhibitors
US9409921B2 (en) 2008-06-27 2016-08-09 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidines as kinase inhibitors
US10596172B2 (en) 2008-06-27 2020-03-24 Celgene Car Llc 2,4-disubstituted pyrimidines useful as kinase inhibitors
US8450335B2 (en) 2008-06-27 2013-05-28 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidines useful as kinase inhibitors
US10010548B2 (en) 2008-06-27 2018-07-03 Celgene Car Llc 2,4-disubstituted pyrimidines useful as kinase inhibitors
US9987276B2 (en) 2008-06-27 2018-06-05 Celgene Car Llc Substituted 2,4-diaminopyrimidines as kinase inhibitors
US8338439B2 (en) 2008-06-27 2012-12-25 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidines useful as kinase inhibitors
CN102203070A (zh) * 2008-09-03 2011-09-28 拜尔农作物科学股份公司 烷氧基-和烷硫基-取代的苯胺基嘧啶类化合物
WO2010025831A1 (de) * 2008-09-03 2010-03-11 Bayer Cropscience Ag Heterozyklisch substituierte anilinopyrimidine als fungizide
WO2010028179A1 (en) * 2008-09-03 2010-03-11 Dr. Reddy's Laboratories Ltd. Heterocyclic compounds as gata modulators
WO2010025833A1 (de) * 2008-09-03 2010-03-11 Bayer Cropscience Ag Alkoxy- und alkylthio-substituierte anilinopyrimidine
US20110245242A1 (en) * 2008-09-03 2011-10-06 Bayer Cropscience Ag Heterocyclically Substituted Anilinopyrimides
US20110245249A1 (en) * 2008-09-03 2011-10-06 Bayer Cropscience Ag Heterocyclically Substituted Anilinopyrimidines
CN102203080A (zh) * 2008-09-03 2011-09-28 拜尔农作物科学股份公司 作为杀菌剂的杂环取代的苯胺基嘧啶
WO2010025863A2 (de) * 2008-09-03 2010-03-11 Bayer Cropscience Ag 4-alkyl-substituierte diaminopyrimidine
WO2010025863A3 (de) * 2008-09-03 2011-03-17 Bayer Cropscience Ag 4-alkyl-substituierte diaminopyrimidine
WO2010025850A1 (de) * 2008-09-03 2010-03-11 Bayer Cropscience Ag Heterozyklisch substituierte anilinopyrimidine als fungizide
US8389717B2 (en) 2008-10-09 2013-03-05 Hoffmann-La Roche Inc. Modulators for amyloid beta
WO2010046034A1 (de) * 2008-10-21 2010-04-29 Bayer Schering Pharma Aktiengesellschaft Sulfonsubsituierte anilino-pyrimidinderivate als cdk-inhibitoren, deren herstellung und verwendung als arzneimittel
EP2179992A1 (de) * 2008-10-21 2010-04-28 Bayer Schering Pharma Aktiengesellschaft Sulfonsubstituierte Anlinopyrimidinderivative als CDK-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel
US8802686B2 (en) 2008-10-21 2014-08-12 Bayer Intellectual Property Gmbh Sulfone-substituted anilinopyrimidine derivatives as CDK inhibitors, the production thereof, and use as a medicine
US8288403B2 (en) 2008-11-10 2012-10-16 Hoffmann-La Roche Inc. Heterocyclic gamma secretase modulators
US9908884B2 (en) 2009-05-05 2018-03-06 Dana-Farber Cancer Institute, Inc. EGFR inhibitors and methods of treating disorders
CN102438993A (zh) * 2009-05-19 2012-05-02 陶氏益农公司 用于控制真菌的化合物和方法
WO2010135070A1 (en) * 2009-05-19 2010-11-25 Dow Agrosciences Llc Compounds and methods for controlling fungi
US8759356B2 (en) 2009-05-19 2014-06-24 Dow Agrosciences, Llc. Compounds and methods for controlling fungi
US8486967B2 (en) 2010-02-17 2013-07-16 Hoffmann-La Roche Inc. Heteroaryl substituted piperidines
US8802674B2 (en) * 2010-06-04 2014-08-12 Genentech, Inc. Aminopyrimidine derivatives as LRRK2 modulators
US8354420B2 (en) 2010-06-04 2013-01-15 Genentech, Inc. Aminopyrimidine derivatives as LRRK2 inhibitors
US20130096102A1 (en) * 2010-06-04 2013-04-18 Genentech, Inc. Aminopyrimidine derivatives as lrrk2 modulators
US8563568B2 (en) 2010-08-10 2013-10-22 Celgene Avilomics Research, Inc. Besylate salt of a BTK inhibitor
US9604936B2 (en) 2010-08-10 2017-03-28 Celgene Car Llc Besylate salt of a BTK inhibitor
US11096942B2 (en) 2010-11-01 2021-08-24 Celgene Car Llc Heterocyclic compounds and uses thereof
US9765038B2 (en) 2010-11-01 2017-09-19 Celgene Car Llc Heteroaryl compounds and uses thereof
US9238629B2 (en) 2010-11-01 2016-01-19 Celgene Avilomics Research, Inc. Heteroaryl compounds and uses thereof
US9867824B2 (en) 2010-11-01 2018-01-16 Celgene Car Llc Heterocyclic compounds and uses thereof
US9375431B2 (en) 2010-11-01 2016-06-28 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidine compounds useful as kinase inhibtors
US8975249B2 (en) 2010-11-01 2015-03-10 Celgene Avilomics Research, Inc. Heterocyclic compounds and uses thereof
US10434101B2 (en) 2010-11-01 2019-10-08 Celgene Car Llc Heterocyclic compounds and uses thereof
US10081606B2 (en) 2010-11-01 2018-09-25 Celgene Car Llc Heteroaryl compounds and uses thereof
US9868723B2 (en) 2010-11-10 2018-01-16 Celgene Car Llc Mutant-selective EGFR inhibitors and uses thereof
US8796255B2 (en) 2010-11-10 2014-08-05 Celgene Avilomics Research, Inc Mutant-selective EGFR inhibitors and uses thereof
US8815882B2 (en) 2010-11-10 2014-08-26 Genentech, Inc. Pyrazole aminopyrimidine derivatives as LRRK2 modulators
EP2468882A1 (de) 2010-12-27 2012-06-27 Bayer CropScience AG Aurorakinaseaktivatorpolypeptide zum Identifizieren von fungizid wirksamen Verbindungen
US9364476B2 (en) 2011-10-28 2016-06-14 Celgene Avilomics Research, Inc. Methods of treating a Bruton's Tyrosine Kinase disease or disorder
US8809331B2 (en) * 2011-11-29 2014-08-19 Genentech, Inc. Aminopyrimidine derivatives as LRRK2 modulators
US20130157999A1 (en) * 2011-11-29 2013-06-20 Genentech, Inc. Aminopyrimidine derivatives as lrrk2 modulators
US9108927B2 (en) 2012-03-15 2015-08-18 Celgene Avilomics Research, Inc. Salts of an epidermal growth factor receptor kinase inhibitor
US9539255B2 (en) 2012-03-15 2017-01-10 Celgene Avilomics Research, Inc. Solid forms of an epidermal growth factor receptor kinase inhibitor
US9056839B2 (en) 2012-03-15 2015-06-16 Celgene Avilomics Research, Inc. Solid forms of an epidermal growth factor receptor kinase inhibitor
US11292772B2 (en) 2012-03-15 2022-04-05 Celgene Car Llc Salts of an epidermal growth factor receptor kinase inhibitor
US10946016B2 (en) 2012-03-15 2021-03-16 Celgene Car Llc Solid forms of an epidermal growth factor receptor kinase inhibitor
US9540335B2 (en) 2012-03-15 2017-01-10 Celgene Avilomics Research, Inc. Salts of an epidermal growth factor receptor kinase inhibitor
US10005738B2 (en) 2012-03-15 2018-06-26 Celgene Car Llc Salts of an epidermal growth factor receptor kinase inhibitor
US10570099B2 (en) 2012-03-15 2020-02-25 Celgene Car Llc Salts of an epidermal growth factor receptor kinase inhibitor
US10004741B2 (en) 2012-03-15 2018-06-26 Celgene Car Llc Solid forms of an epidermal growth factor receptor kinase inhibitor
US9126950B2 (en) 2012-12-21 2015-09-08 Celgene Avilomics Research, Inc. Heteroaryl compounds and uses thereof
US9549927B2 (en) 2012-12-21 2017-01-24 Celgene Avilomics Research, Inc. Heteroaryl compounds and uses thereof
US9980964B2 (en) 2013-02-08 2018-05-29 Celgene Car Llc ERK inhibitors and uses thereof
US9504686B2 (en) 2013-02-08 2016-11-29 Celgene Avilomics Research, Inc. ERK inhibitors and uses thereof
US9145387B2 (en) 2013-02-08 2015-09-29 Celgene Avilomics Research, Inc. ERK inhibitors and uses thereof
US9561228B2 (en) 2013-02-08 2017-02-07 Celgene Avilomics Research, Inc. ERK inhibitors and uses thereof
US9796700B2 (en) 2013-02-08 2017-10-24 Celgene Car Llc ERK inhibitors and uses thereof
US9492471B2 (en) 2013-08-27 2016-11-15 Celgene Avilomics Research, Inc. Methods of treating a disease or disorder associated with Bruton'S Tyrosine Kinase
US9415049B2 (en) 2013-12-20 2016-08-16 Celgene Avilomics Research, Inc. Heteroaryl compounds and uses thereof
US9783505B2 (en) 2013-12-20 2017-10-10 Signal Pharmaceuticals, Llc Substituted diaminopyrimidyl compounds, compositions thereof, and methods of treatment therewith
US9556126B2 (en) 2013-12-20 2017-01-31 Signal Pharmaceuticals, Llc Substituted diaminopyrimidyl compounds, compositions thereof, and methods of treatment therewith
US10202364B2 (en) 2014-08-13 2019-02-12 Celgene Car Llc Forms and compositions of an ERK inhibitor
US10005760B2 (en) 2014-08-13 2018-06-26 Celgene Car Llc Forms and compositions of an ERK inhibitor

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CO6210776A2 (es) 2010-10-20
CN101621927A (zh) 2010-01-06
BRPI0808433A2 (pt) 2014-07-29
TW200900386A (en) 2009-01-01
MX2009008700A (es) 2009-08-27
EA015174B1 (ru) 2011-06-30
EA200901187A1 (ru) 2010-02-26
US20100081679A1 (en) 2010-04-01
AU2008224150A1 (en) 2008-09-12
CA2679488A1 (en) 2008-09-12
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EP2129222A1 (de) 2009-12-09
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